diff --git a/src/Illuminate/Http/Client/PendingRequest.php b/src/Illuminate/Http/Client/PendingRequest.php
index f987f0aed653..307e51476931 100644
--- a/src/Illuminate/Http/Client/PendingRequest.php
+++ b/src/Illuminate/Http/Client/PendingRequest.php
@@ -2,6 +2,7 @@
 
 namespace Illuminate\Http\Client;
 
+use Exception;
 use GuzzleHttp\Client;
 use GuzzleHttp\Cookie\CookieJar;
 use GuzzleHttp\Exception\ConnectException;
@@ -715,7 +716,13 @@ public function send(string $method, string $url, array $options = [])
                     $this->populateResponse($response);
 
                     if (! $response->successful()) {
-                        $shouldRetry = $this->retryWhenCallback ? call_user_func($this->retryWhenCallback, $response->toException()) : true;
+                        try {
+                            $shouldRetry = $this->retryWhenCallback ? call_user_func($this->retryWhenCallback, $response->toException()) : true;
+                        } catch (Exception $exception) {
+                            $shouldRetry = false;
+
+                            throw $exception;
+                        }
 
                         if ($attempt < $this->tries && $shouldRetry) {
                             $response->throw();
diff --git a/tests/Http/HttpClientTest.php b/tests/Http/HttpClientTest.php
index 5a528d4445de..7c4eb54f939a 100644
--- a/tests/Http/HttpClientTest.php
+++ b/tests/Http/HttpClientTest.php
@@ -2,6 +2,7 @@
 
 namespace Illuminate\Tests\Http;
 
+use Exception;
 use GuzzleHttp\Middleware;
 use GuzzleHttp\Promise\PromiseInterface;
 use GuzzleHttp\Psr7\Response as Psr7Response;
@@ -1271,6 +1272,31 @@ public function testRequestExceptionIsNotThrownWithoutRetriesIfRetryNotNecessary
         $this->factory->assertSentCount(1);
     }
 
+    public function testExceptionThrownInRetryCallbackWithoutRetrying()
+    {
+        $this->factory->fake([
+            '*' => $this->factory->response(['error'], 500),
+        ]);
+
+        $exception = null;
+
+        try {
+            $this->factory
+                ->retry(2, 1000, function ($exception) use (&$whenAttempts) {
+                    throw new Exception('Foo bar');
+                }, false)
+                ->get('http://foo.com/get');
+        } catch (Exception $e) {
+            $exception = $e;
+        }
+
+        $this->assertNotNull($exception);
+        $this->assertInstanceOf(Exception::class, $exception);
+        $this->assertEquals('Foo bar', $exception->getMessage());
+
+        $this->factory->assertSentCount(1);
+    }
+
     public function testMiddlewareRunsWhenFaked()
     {
         $this->factory->fake(function (Request $request) {